IMPPAT Phytochemical information: 
Pinnarine

Pinnarine
Summary

SMILES: O[C@@H]1/C=C/[C@H](C)[C@H]2CCC[C@@]32CCC[C@@H](N3)C/C=C(/C(=O)OCC/C(=C/1)/Cl)\C
InChI: InChI=1S/C23H34ClNO3/c1-16-8-10-20(26)15-18(24)11-14-28-22(27)17(2)7-9-19-5-3-12-23(25-19)13-4-6-21(16)23/h7-8,10,15-16,19-21,25-26H,3-6,9,11-14H2,1-2H3/b10-8+,17-7+,18-15-/t16-,19+,20+,21+,23+/m0/s1
InChIKey: YETAKRZPZUKKMS-IBSBDYNISA-N
DeepSMILES: O[C@@H]/C=C/[C@H]C)[C@H]CCC[C@]5CCC[C@@H]N6)C/C=C/C=O)OCC/C=C/%22)/Cl))))))\C
Scaffold Graph/Node/Bond level: O=C1C=CCC2CCCC3(CCCC3CC=CCC=CCCO1)N2
Scaffold Graph/Node level: OC1CCCC2CCCC3(CCCC3CCCCCCCCO1)N2
Scaffold Graph level: CC1CCCCCCCCCC2CCCC23CCCC(CCC1)C3
Functional groups: CO; C/C=C/C; CNC; C/C=C(\C)C(=O)OC; C/C(Cl)=C/C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Macrolides and analogues
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
pinnarin
External chemical identifiers:
CID:CID_53356216; ChEBI:CHEBI:68106
Chemical structure download


Pinnarine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 407.98
Log P RDKit 4.63
Topological polar surface area (Å2) RDKit 58.56
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Pinnarine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.45


Pinnarine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.56
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes